October 14

When I Paint My Masterpiece: Guitar Solo



When I Paint My Masterpiece

Jerry Garcia Guitar Solo 10/3/87

Bob Dylan wrote “When I Paint My Masterpiece” in 1971. The Band delivered the first recorded version of the song on their 1971 album "Cahoots," with Dylan’s rendition appearing a few months later on Bob Dylan’s "Greatest Hits Vol. II." Although Jerry Garcia had been performing “When I Paint My Masterpiece” as early as 1972 with his solo projects, the Grateful Dead didn't add the song to their repertoire until 1987. The solo taught in this lesson comes from 10/3/87, and can be found on "View from the Vault III."


A Myriad of Masterpieces

One thing that makes this song so interesting is that everyone played it a little bit different. Let’s begin with Dylan’s version. Dylan plays “Masterpiece” in the key of A, which later modulates up a half-step to the key of Bb. The song fits an AABA form, with each section lasting 8 bars. In the A sections, Dylan goes to the V chord for just one bar, whereas the Dead play the V chord for two bars. After the first time through the form, Dylan’s version has a four bar interlude 

Bob Dylan Greatest Hits Volume 2

on the I chord (A) before launching into the second time through the progression. After the second time through the form, Dylan modulates up a half-step via the V chord (F), which lasts two bars and sets up the same 32 bar form, now in the key of Bb. After one time through the form in this new key, Dylan’s version comes to an end.

Playin' In The Band

The Band’s version of “Masterpiece” is played in the Key of Bb, but does not modulate (I’m not counting the bridge which I’ll address in a moment) the way the Dylan (and Dead’s) version does. The A sections of this version resemble how the Dead play the A sections. After the first time through the 32 bar form, The 

The Band

Saugerties, NY: 1968. The Band behind Big Pink‚ Easter Sunday, West Saugerties. Robbie Robertson, Richard Manuel, Rick Danko, Garth Hudson, Levon Helm. ©Elliott Landy / The Image Works

Band’s version features an 8 bar interlude that alternates between two bars of the IV chord (Eb) and two bars of the I chord (Bb). After the second time through the form, the band adds two more bars of the I chord before going to a bridge section that isn’t found in Dylan or the Dead’s version of the song (“Sailing ‘round the world in a dirty gondola…”). The bridge is 12 bars long, and goes through the following chord changes: 

The Band Bridge Section

After the bridge, the Band’s version goes through the 32 bar form one more time, in the original key of Bb. After this last time through the form, the Band plays the 8 bar interlude they played after the first time through before fading out.

Playing Dead

That brings us to the Grateful Dead’s rendition of “Masterpiece.” The Dead chose to play the song in the Key of G, and then they modulate up a whole-step, to the key of A after the main guitar solo. Here’s the complete form:

Intro (varying lengths)
32 bar AABA form
8 bar interlude (A section - one time through)
32 bar form
Guitar Solo (played over the 32 bar form)
Modulation up a whole-step (2 bars of A)
32 bar form (now in the key of A)
A section
2nd half of A section |E | % | A | % |
End on an A chord

Here is the 32 bar form in which the guitar solo is played over:

Masterpiece Chord Chart

Once again, Jerry uses chord shapes as a foundation to play through the chord changes. Once you get this solo under your fingers, work on taking a few of your favorite phrases and coming up with your own variations and melodies. Most of all, have fun!


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